Skip to main content
Log in

Thermodynamic study on the interaction of imidazolium salts and POE-type nonionic surfactant in the adsorbed film

  • Original Contribution
  • Published:
Colloid and Polymer Science Aims and scope Submit manuscript

Abstract

The composition of the adsorbed film and the excess Gibbs energy of adsorption \( {\widehat{g}}^{\mathrm{H},\mathrm{E}} \) were evaluated from thermodynamic analysis of surface tensions for the 1-decyl-3-methylimidazoulium bromide (C10mimBr)–tetraethylene glycol monooctyl ether (C8E4) and 1-decyl-3-methyl-imidazolium tetrafluorobrorate (C10mimBF4)–C8E4 systems, where the counter anion of imidazolium salts is different from each other. The higher miscibility of two components compared to an ideal mixing and thus negative \( {\widehat{g}}^{\mathrm{H},\mathrm{E}} \) were observed in the former, which comes from the ion–dipole interaction between imidazolium cation and the oxyethylene group of C8E4. On the other hand, the lower miscibility and thus positive \( {\widehat{g}}^{\mathrm{H},\mathrm{E}} \) were observed for the latter. Such differences were attributed to that BF4 forms two hydrogen bonds and has stronger affinity with the cationic head group of C10mim+ than Br. This results in that the ion–dipole interaction between C8E4 and C10mim+ cation is diminished in the C10mimBF4–C8E4 system.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Rogers RD, Seddon KR (2003) Ionic liquids—solvents of the future? Science 302:792–793

    Article  Google Scholar 

  2. Hallett JP, Welton T (2011) Room-temperature ionic liquids: solvents for synthesis and catalysis 2. Chem Rev 111:3508–3576

    Article  CAS  Google Scholar 

  3. Łuczak J, Hupka J, Thöming J, Jungnickel C (2008) Self-organization of imidazolium ionic liquids in aqueous solution. Colloids and Surfaces A: Physicochem Eng Aspects 329:125–133

    Article  Google Scholar 

  4. Dong B, Li N, Zheng LQ, Yu L, Inoue T (2007) Surface adsorption and micelle formation of surface active ionic liquids in aqueous solution. Langmuir 23:4178–4182

    Article  CAS  Google Scholar 

  5. Kempter V, Kirchner B (2010) The role of hydrogen atoms in interactions involving imidazolium-based ionic liquids. J Mol Struct 972:22–34

    Article  CAS  Google Scholar 

  6. Anderson JL, Pino V, Hagberg EC, Sheares VV, Armstrong DW (2003) Surfactant solvation effects and micelle formation in ionic liquids. Chem Commun 19:2444–2445

    Article  Google Scholar 

  7. Fletcher KA, Pandey S (2004) Surfactant aggregation within room-temperature ionic liquid 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Langmuir 20:33–36

    Article  CAS  Google Scholar 

  8. Tran CD, Yu S (2005) Near-infrared spectroscopic method for the sensitive and direct determination of aggregations of surfactants in various media. J Colloid Interface Sci 283:613–618

    Article  CAS  Google Scholar 

  9. Patrascu C, Gauffre F, Nallet F, Bordes R, Oberdisse J, de Lauth-Viguerie N, Mingotaud C (2006) Micelles in ionic liquids: aggregation behavior of alkylpoly(ethyleneglycol)-ethers in1-butyl-3-methyl-imidazolium type ionic liquids. ChemPhysChem 7:99–101

    Article  CAS  Google Scholar 

  10. Inoue T, Yamakawa H (2011) Micelle formation of nonionic surfactants in a room temperature ionic liquid,1-butyl-3-methylimidazolium tetrafluoroborate: surfactant chain length dependence of the critical micelle concentration. J Colloid Interface Sci 356:798–802

    Article  CAS  Google Scholar 

  11. Inoue T, Misono T (2008) Cloud point phenomena for POE-type nonionic surfactants in a model room temperature ionic liquid. J Colloid Interface Sci 326:483–489

    Article  CAS  Google Scholar 

  12. Gao YA, Zhang J, Xu HY, Zhao XY, Zheng LQ, Li XW, Yu L (2006) Structural studies of 1-butyl-3-methylimidazolium tetrafluoroborate/TX-100/p-xylene ionic liquid microemulsions. ChemPhysChem 7:1554–1561

    Article  CAS  Google Scholar 

  13. Gao YA, Li N, Zheng LQ, Zhao XY, Zhang SH, Han BX, Hou WG, Li GZ (2006) A cyclic voltammetric technique for the detection of micro-regions of bmimPF6/Tween 20/H2O microemulsions and their performance characterization by UV–vis spectroscopy. Green Chem 8:43–49

    Article  CAS  Google Scholar 

  14. Gao Y, Han SB, Han BX, Li GZ, Shen D, Li ZH, Du JM, Hou WG, Zhang GY (2005) TX-100/Water/1-butyl-3-methylimidazolium hexafluorophosphate microemulsions. Langmuir 21:5681–5684

    Article  CAS  Google Scholar 

  15. Eastoe J, Gold S, Rogers SE, Paul A, Welton T, Heenan RK, Grillo I (2005) Ionic liquid-in-oil microemulsions. J Am Chem Soc 127:7302–7303

    Article  CAS  Google Scholar 

  16. Zhang S, Gao Y, Dong B, Zheng L (2010) Interaction between the added long-chain ionic liquid 1-dodecyl-3-methylimidazolium tetrafluoroborate and Triton X-100 in aqueous solutions. Colloids and Surfaces A: Physicochem Eng Aspects 327:182–189

    Article  Google Scholar 

  17. Gao F, Hu J, Peng CJ, Liu HL, Hu Y (2012) Synergic effects of imidazolium ionic liquids on p123 mixed micelles for inducing micro/mesoporous materials. Langmuir 28:2950–2959

    Article  CAS  Google Scholar 

  18. Dong K, Zhang S, Wang D, Yao X (2006) Hydrogen bonds in imidazolium ionic liquids. J Phys Chem A 110:9775–9782

    Article  CAS  Google Scholar 

  19. Goodchild I, Collier L, Millar SL, Prokeš I, Lord JCD, Butts CP, Bowers J, Webster JRP, Heenan RK (2007) Structural studies of the phase, aggregation and surface behaviour of 1-alkyl-3-methylimidazolium halide + water mixtures. J Colloid Interface Sci 303:455–468

    Article  Google Scholar 

  20. Shimamoto K, Onohara A, Takumi H, Wantanabe I, Tanida H, Matsubara H, Takiue T, Aratono M (2009) Miscibility and distribution of counterions of imidazolium ionic liquid mixtures at the air/water surface. Langmuir 25:9954–9959

    Article  CAS  Google Scholar 

  21. Jeon Y, Sung J, Bu W, Vaknin D, Ouchi Y, Kim D (2008) Interfacial restructuring of ionic liquids determined by sum-frequency generation spectroscopy and x-ray reflectivity. J Phys Chem C 112:19649–19654

    Article  CAS  Google Scholar 

  22. Wu J, Li N, Zheng L, Li X, Gao Y, Inoue T (2008) Aggregation behavior of polyoxyethylene (20) sorbitan monolaurate (tween 20) in imidazolium based ionic liquids. Langmuir 24:9314–9322

    Article  CAS  Google Scholar 

  23. Li HH, Imai Y, Takiue T, Matsubara H, Aratono M (2013) Effect and mixing of counter anions at the surface of aqueous solution of imidazolium-based ionic liquids. Colloids and Surfaces A: Physicochem Eng Aspects 427:26–32

    Article  CAS  Google Scholar 

  24. Matsuda T, Asoh Y, Villeneuve M, Matsubara H, Takiue T, Aratono M (2004) Nonideal mixing of dodecyltrimethylammonium halides and nonionic surfactant in adsorbed films and micelles. Colloid Polym Sci 282:324–329

    Article  CAS  Google Scholar 

  25. Matsubara H, Ohta A, Kaneda M, Ikeda N, Aratono M (2000) Interaction between ionic and nonionic surfactants in the adsorbed film and micelle. dodecylammonium chloride and tetraethylene glycol monooctyl ether. Langmuir 16:7589–7596

    Article  CAS  Google Scholar 

  26. Matsubara H, Muroi S, Kameda M, Ikeda N, Ohta A, Aratono M (2001) Interaction between ionic and nonionic surfactants in the adsorbed film and micelle. 3. Sodium dodecyl sulfate and tetraethylene glycol monooctyl ether. Langmuir 17:7752–7757

    Article  CAS  Google Scholar 

  27. Matsubara H, Eguchi T, Takumi H, Tsuchiya K, Takiue T, Aratono M (2009) Surface adsorption and aggregate formation of cationic gemini surfactant and long-chain alcohol mixtures. J Phys Chem B 113:884–8853

    Article  Google Scholar 

  28. Aratono M, Villeneuve M, Takiue T, Ikeda N, Iyota H (1998) Thermodynamic consideration of mixtures of surfactants in adsorbed films and micelles. J Colloid Interface Sci 200:161–171

    Article  CAS  Google Scholar 

  29. Nockemann P, Binnemans K, Driesen K (2005) Purification of imidazolium ionic liquids for spectroscopic applications. Chem Phys Lett 415:131–136

    Article  CAS  Google Scholar 

  30. Schubert KV, Stery R, Kahlweit M (1991) A new purification technique for alkyl polyglycol ethers and miscibility gaps for water-CiEi. J Colloid Interface Sci 141:21–29

    Article  CAS  Google Scholar 

  31. Thomaier S, Kunz W (2007) Aggregates in mixtures of ionic liquids. J Mol Liq 130:104–107

    Article  CAS  Google Scholar 

  32. Headley AD, Kotti SRSS, Nam J, Li K (2005) Effect of hydrophobic side-chains on the salvation of imidazolium salts. J Phys Org Chem 18:1018–1022

    Article  CAS  Google Scholar 

  33. Tsuzuki S, Tokuda H, Hayamizu K, Watanabe M (2005) Magnitude and directionality of interaction in ion pairs of ionic liquids: relationship with ionic conductivity. J Phys Chem B 109:16474–16481

    Article  CAS  Google Scholar 

  34. Israelachvili JN (1992) Intermolecular and surface forces, 2nd edn. Academic, London

    Google Scholar 

  35. Dieter KM, Dymek CJ, Heimer NE, Rovang JW, Wilkes JS (1988) Ionic structure and interactions in 1-methyl-3-ethylimidazolium chloride-AlCl3 molten salts. J Am Chem Soc 110:2722–2726

    Article  CAS  Google Scholar 

  36. Talaty ER, Raja S, Storhaug VJ, Dolle A, Carper WR (2004) Raman and infrared spectra and ab initio calculations of c2-4mim imidazolium hexafluorophosphate ionic liquids. J Phys Chem B 108:13177–13184

    Article  CAS  Google Scholar 

  37. Li HH, Imai Y, Yamanaka M, Hayami Y, Takiue T, Mstsubara H, Aratono M (2011) Specific counterion effect on the adsorbed film of cationic surfactant mixtures at the air/water interface. J Colloid Interface Sci 359:189–193

    Article  CAS  Google Scholar 

  38. Villeneuve M, Ikeda N, Motomura K, Aratono M (1998) Miscibility of butanol and cationic surfactant in the adsorbed film and micelle. J Colloid Interface Sci 208:388–398

    Article  Google Scholar 

  39. Takumi H, Imai Y, Toh N, Matsubara H, Takiue T, Aratono M (2014) Miscibility of imidazolium and pyridinium ionic liquids including BF4 at the air/water interface. Colloids and Surfaces A: Physicochem Eng Aspects 441:59–65

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Makoto Aratono.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Li, H., Imai, Y., Takiue, T. et al. Thermodynamic study on the interaction of imidazolium salts and POE-type nonionic surfactant in the adsorbed film. Colloid Polym Sci 292, 1209–1215 (2014). https://doi.org/10.1007/s00396-014-3172-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00396-014-3172-5

Keywords

Navigation